2346-74-9

Basic information

• Product Name: 6-CHLORO-9-METHYLPURINE
• Synonyms: OTAVA-BB BB7216640145;6-CHLORO-9-METHYL-9H-PURINE;6-CHLORO-9-METHYLPURINE;9-METHYL-6-CHLOROPURINE;AKOS BBS-00003131;IFLAB-BB F1371-0159;NSC 4948
• CAS NO: 2346-74-9
• Molecular Formula: C₆H₅ClN₄
• Molecular Weight: 168.58
• Product Categories: pharmacetical;Nucleotides and Nucleosides;Bases & Related Reagents;Nucleotides
• Mol File: 2346-74-9.mol

Chemical Properties

• Melting Point: 129-134oC
• Boiling Point: 321.7 °C at 760 mmHg
• Flash Point: 148.4 °C
• Appearance: pale yellow solid
• Density: 1.59 g/cm³
• Vapor Pressure: 0.000293mmHg at 25°C
• Refractive Index: 1.743
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility: Chloroform (Slightly), Ethyl Acetate (Slightly)
• PKA: 1.26±0.10(Predicted)
• CAS DataBase Reference: 6-CHLORO-9-METHYLPURINE(CAS DataBase Reference)
• NIST Chemistry Reference: 6-CHLORO-9-METHYLPURINE(2346-74-9)
• EPA Substance Registry System: 6-CHLORO-9-METHYLPURINE(2346-74-9)

Safety Data

• Hazardous Substances Data: 2346-74-9(Hazardous Substances Data)

Usage

Uses

1. Used in Pharmaceutical Industry:
6-CHLORO-9-METHYLPURINE is used as a synthetic intermediate for the development of various pharmaceutical compounds. Its unique chemical structure allows it to be a key component in the synthesis of drugs targeting specific biological pathways.
2. Used in Chemical Research:
6-CHLORO-9-METHYLPURINE is also utilized in chemical research as a starting material for the synthesis of novel compounds with potential applications in various fields, including materials science, agrochemistry, and environmental science.
3. Used in Biochemical Studies:
Due to its structural similarity to purine, 6-CHLORO-9-METHYLPURINE can be employed in biochemical studies to investigate the effects of structural modifications on the biological activity of purine-based compounds. This can lead to a better understanding of the molecular mechanisms underlying various biological processes and the development of targeted therapeutics.

Synthesis Reference(s)

Journal of the American Chemical Society, 79, p. 490, 1957 DOI: 10.1021/ja01559a069

InChI:InChI=1/C6H5ClN4/c1-11-3-10-4-5(7)8-2-9-6(4)11/h2-3H,1H3

Upstream product

• 122-51-0 orthoformic acid triethyl ester 
• 52602-68-3 6-chloro-N⁴-methylpyrimidine-4,5-diamine 
• 87-42-3 6-chloropurine 
• 74-88-4 methyl iodide 
• 67-56-1 methanol 
• 87-42-3 6-chloro-7H-purine 
• 74-83-9 methyl bromide 
• 74-87-3 methylene chloride 

Downstream Products

• 35234-62-9 6-Propylamino-9-methylpurin 
• 1127-75-9 9-methyl-6-methylthiopurine 
• 5400-01-1 N⁶-ethyl-9-methyladenine 
• 3013-82-9 6-N,N-dimethyl-9-methyladenine 
• 5418-12-2 isopropyl-(9-methyl-9H-purin-6-yl)-amine 
• 1006-20-8 9-methyl-1,9-dihydro-6H-purine-6-thione 
• 2009-52-1 N₆,N₉-dimethyladenine 
• 100124-22-9 6-(4-bromo-phenoxy)-9-methyl-9H-purine 
• 5401-70-7 9-methyl kinetin 
• 109292-99-1 (9-Methyl-9H-purin-6-yl)-(2-thiophen-3-yl-ethyl)-amine 
• 109292-95-7 N₆-2-Fluorophenyl-9-methyladenine 
• 109293-01-8 N⁶-(1-phenyl-2(S)-propyl)-9-methyladenine 
• 135394-02-4 (2,2-Diphenyl-ethyl)-(9-methyl-9H-purin-6-yl)-amine 
• 109293-00-7 N⁶-(1-phenyl-2(R)-propyl)-9-methyladenine 

Relevant articles and documents

Synthesis of N6-[endo-2′-(endo-5′-hydroxy)norbornyl] -8-(N-methylisopropylamino)-9-methyladenine (WRC-0571): A potent and selective adenosine A1 receptor antagonist

A new versatile synthesis of N6-[endo-2′-(endo-5′- hydroxy)norbornyl]-8-(N-methylisopropylamino)-9-methyladenine (WRC-0571), a highly potent and selective antagonist for adenosine A1 receptor, is presented. The overall yield is 14%.

A novel noninvasive method for assessing glutathione-conjugate efflux systems in the brain

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Mechanism of Action of the Cytotoxic Asmarine Alkaloids

The asmarines are a family of cytotoxic natural products whose mechanism of action is unknown. Here, we used chemical synthesis to reverse engineer the asmarines and understand the functions of their individual components. We found that the potent asmarine analog delmarine arrested the mammalian cell cycle in the G1 phase and that both cell cycle arrest and cytotoxicity were rescued by cotreatment with ferric and ferrous salts. Cellular iron deprivation was clearly indicated by changes in iron-responsive protein markers, and cytotoxicity occurred independently of radical oxygen species (ROS) production. Chemical synthesis allowed for annotation of the distinct structural motifs required for these effects, especially the unusual diazepine, which we found enforced an iron-binding tautomer without distortion of the NCNO dihedral angle out of plane. With this information and a correlation of cytotoxicity with logP, we could replace the diazepine by lipophilic group appendage to N9, which avoided steric clash with the N6-alkyl required to access the aminopyridine. This study transformed the asmarines, scarce marine metabolites, into easily synthesized, modular chemotypes that may complement or succeed iron-selective binders in clinical trials and use.

Regioselective alkylation reaction of purines under microwave irradiation

The alkylation of purines which is generally carried out after anion formation by treatment with a base and alkyl halide is complicated and in the best cases, mixtures of N-alkylated compounds are obtained. Purine derivatives can be acquired from alkylati

Synthesis of novel selenotetrazole purine derivatives and their potential chemotherapeutic activities

The development of novel chemotherapeutic agents is indispensable to improve cancer treatment. One of the conventional approaches toward the synthesis of anticancer agents is the design of a compound whose structure is similar to purines found in DNA. In this study, a series of novel artificial purine nucleosides bearing selenotetrazole pharmacophore, 4a–4h, were synthesized. In order to get preliminary information about their cytotoxic activities, the interaction of compounds with DNA was investigated by UV titration and agarose gel electrophoresis and transcription inhibition studies were performed. The cytotoxic effects of the compounds against B16 melanoma, OV90 ovarian cancer, JM1 lymphoma cell lines, and PHA-induced peripheral blood lymphocytes were also investigated. In cell assay studies, the effects of the compounds on synthesis and mitosis stage of cell cycle were compared by flow cytometry. Although none of the compounds synthesized interacted with DNA and exhibited transcription inhibition, all of them significantly inhibited DNA synthesis phase and showed cytotoxic activity on cancer and proliferating cells. [Figure not available: see fulltext.]

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The approvals of idelalisib and duvelisib have validated PI3Kδinhibitors for the treatment for hematological malignancies driven by the PI3K/AKT pathway. Our program led to the identification of structurally distinct heterocycloalkyl purine inhibitors wit

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